Brian Cashman, General Manager/Senior Vice President of the New York Yankees is seen before the start of his team's game against the Cleveland Indians at Yankees Stadium on June 3, 2013 in the Bronx, NY

As any sports fan—or reader of New York tabloids—is sure to be aware at this point, New York Yankees General Manager Brian Cashman stirred up a media firestorm when he reacted strongly to a tweet from Alex Rodriguez in which the Yankees third baseman proclaimed that his doctor had cleared him for game action. Here’s what Cashman said to ESPN New York’s Andrew Marchard: “You know what, when the Yankees want to announce something, [we will]. Alex should just shut the f— up. That’s it. I’m going to call Alex now.” The diatribe had exactly the effect you would expect it to have, spawning back page headlines, countless columns and wild conspiracy theories about Rodriguez’s future in New York. But here’s the craziest thing about Cashman’s comments: It’s completely in character for the Yankees GM. Maybe the on-the-record profanity is a new one for Cashman, but he’s been saying and doing outlandish things for years.

Cashman was named the Yankees general manager in 1998—he was just 31 years old at the time. During his tenure, the Yankees have won four World Series and six American League pennants. In most cases, a track record like that would make a general manager the toast of baseball. That hasn’t been the case for Cashman. Instead, most of the credit for those championships has gone to the players (Derek Jeter, Mariano Rivera, Jorge Posada, etc.), managers (Joe Torre and Joe Girardi) and enormous payroll (regularly the largest in baseball by a considerable margin). So perhaps it is for this reason—or another entirely—that Cashman started to behave a little… untraditionally during the latter half of his tenure.

General managers in baseball—well, basically any sport—are typically characterized by their benign comments in the press and reluctance to spend time in the limelight. Though there are certainly exceptions to that rule, Cashman was an unlikely candidate to become a multiple-time winner of the Outspoken GM of the Year award. He was promoted at a remarkably young age by the the sport’s most storied and traditional franchise, which already had a legendarily volatile owner. Not to mention the fact that he, quite frankly, looks more like an accountant than a stereotypical baseball man. And yet Cashman has made headline after headline for his outlandish behavior and comments. Here’s an abbreviated timeline:

2006: Radio talk shows have always played a prominent role in the New York sports scene, perhaps none more so than Mike and the Mad Dog, featuring opinionated co-hosts Mike Francesca and Chris “Mad Dog” Russo. When Cashman appeared on the show in the summer of 2006 just after the Yankees had acquired starting pitcher Cory Lidle, Russo criticized the trade. That did not sit especially well with Cashman. The GM told Russo “not to embarrass himself,” repeatedly called him unprofessional and said, “I’m biting my tongue because you are irritating the heck out of me.” Though outspoken, this particular interview would prove to be on the tame end of the Cashman spectrum in subsequent years.

2008: After a difficult season that saw the Yankees limp to 3rd place in the American League East and public criticism of new manager Joe Girardi from Cashman, the GM had his contract renewed by Hank and Hal Steinbrenner. Instead of showing humility and confidence, Cashman lashed out at the media when announcing his new contract: “I’m a competitive person and I don’t like what I see sometimes that shows up in the newspapers… And the story line that was going to be written if I left I didn’t agree with. And I’m not going to let that story be written.”

2010: Though Cashman hadn’t made many headlines since signing his extension in ’08, that changed during the 2010-2011 offseason. Derek Jeter’s contract was up and the Yankees legend was expected to re-sign with the club. But Cahsman made it clear that he wasn’t going to overpay for the aging star to stay with the franchise that drafted him. “We’re not just going to write a blank check,” Cashman said. “We’ve encouraged him to test the market and see if there’s something he would prefer other than this. If he can, fine.” This is not how general managers discuss beloved stars, but Cashman has shown little regard for what’s expected of him. To that end, two weeks later, Cashman described himself as the Yankees’ “director of spending.” Though not inaccurate, the comment may have hit a little close to home for Yankees brass and fans who have grown sensitive about the team’s bloated payroll. Oh, and the same week he made those comments, he scaled a 22-story building in Stamford, Conn. while wearing “reindeer antlers on top of a wig of spiked hair.”

2011: To kick off the new year, Cashman tended bar in New York City dressed like this. In April, he criticized the Mets’ usage of reviever Pedro Feliciano over the three previous seasons (the Yankees signed the southpaw before the 2011 campaign), saying that Feliciano was “abused.” Criticizing one’s own team or players in public is rare enough, but to make comments like these on the record about the habits of other teams is all but unheard of—save in the world of Cashman. That very same week, the Yankees were embroiled in a sign-stealing controversy, leading Cashman to lash out at fans discussing the particulars on the Internet. “It’s probably more work talking about it than it’s worth, and anybody obsessed about it yesterday I kind of feel are psycho,” he said. “The psychotics that obsessed about it all day, I think we did them all a favor by keeping them off the street preventing them from hurting others.”

Later in the season, Cashman continued on his apparent mission to alienate the franchise’s most beloved players, this time by sparring with Jorge Posada in the press. When Girardi dropped the aging catcher to ninth in the batting order for a game in mid-May, Posada reportedly pulled himself from the lineup. That decision inspired Cashman to say, “Jorge had to deal with a situation he created by himself.” Then Posada fired back: “I don’t know why he made a statement during the game… I don’t understand that. That’s the way he works now.” Cashman added even more fuel to the fire by saing, “I think Jorge has some damage control to deal with, and I hope he deals with it the best way possible.”

2012: Because his own players, coaches and hometown rivals didn’t seem like enough factions to alienate, Cashman then set his sights on division rivals Tampa Bay. Before the start of the 2012 season, he told reporters that the Yankees “conceded” the American League East division title to the Rays in 2010 because it meant “nothing more than a t-shirt and hat.” It takes some serious gumption to tell a team that finished ahead of you that they were only able to do so because that’s the way you wanted it to go down—not to mention the fact that the statement came nearly 18 months after the fact.

Later that spring, Cashman went back to trolling closer to home, telling reporters all about how long-time Yankees starter Andy Pettite cost himself roughly $10 million by waffling on a return to baseball. After offering a $12 million contract at the end of the 2011 season, the Yankees were able to sign Pettite for just $2.5 million during spring training. Of course, no one would have known the particulars of the initial offer—or what led to the final deal—had Cashman not taken the opportunity to keep it real.

And now here we are again during the 2013 season, with more Cashman-created headlines on the back pages of the New York tabloids. Though some might call this pattern of behavior petty or misguided, it’s hard to deny that Cashman’s antics are rather entertaining (with a few obvious exceptions). Over the last 15 years, it’s become clear that there’s virtually nothing he can say to jeopardize his job with the Yankees, so there appears little reason for him to let up now. All we can do is wait and see what he cooks up next for the back page of the New York Post.